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  • 873-75-6 Structure
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    1. Product Name: 4-Bromobenzyl alcohol
    2. Synonyms: 4-BROMOBENZYL ALCOHOL;RARECHEM AL BD 0075;P-BROMOBENZYL ALCOHOL;(4-Bromophenyl)methanol;Benzyl alcohol, p-bromo-;4-Brom-benzyl alcohol;Brombenzylalcohol;4-BROMOBENZYL ALCOHOL 98%
    3. CAS NO:873-75-6
    4. Molecular Formula: C7H7BrO
    5. Molecular Weight: 187.03
    6. EINECS: 212-851-7
    7. Product Categories: Benzhydrols, Benzyl & Special Alcohols;Alcohol;Alcohols;Bromine Compounds;C7 to C8;Oxygen Compounds
    8. Mol File: 873-75-6.mol
    9. Article Data: 264
  • Chemical Properties

    1. Melting Point: 75-77 °C(lit.)
    2. Boiling Point: 220.79°C (rough estimate)
    3. Flash Point: 115.7 °C
    4. Appearance: White to slightly beige/Crystals or Crystalline Powder
    5. Density: 1.3839 (rough estimate)
    6. Vapor Pressure: 0.00397mmHg at 25°C
    7. Refractive Index: 1.5840 (estimate)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: dioxane: soluble1g/10 mL, clear to faintly turbid, colorless to
    10. PKA: 14.16±0.10(Predicted)
    11. Water Solubility: 2.31g/L at 20℃
    12. BRN: 1931620
    13. CAS DataBase Reference: 4-Bromobenzyl alcohol(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Bromobenzyl alcohol(873-75-6)
    15. EPA Substance Registry System: 4-Bromobenzyl alcohol(873-75-6)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 873-75-6(Hazardous Substances Data)

873-75-6 Usage

Description

4-Bromobenzyl alcohol is an organic compound that serves as a key intermediate in the synthesis of various polymers and organic compounds. It is known for its ability to undergo different chemical reactions, such as three-component reactions, oxidation reactions, and trimethylsilylation reactions, making it a versatile building block in organic chemistry.

Uses

Used in Polymer Synthesis:
4-Bromobenzyl alcohol is used as a monomer in the synthesis of hydroxyl end functionalized substituted polyfluorene, which is an important class of conjugated polymers with potential applications in optoelectronic devices, such as light-emitting diodes (LEDs) and field-effect transistors (FETs).
Used in Amphiphilic Polymers:
4-Bromobenzyl alcohol is used as a monomer in the synthesis of amphiphilic polymers, which are copolymers with both hydrophilic and hydrophobic segments. These polymers are used in various applications, such as drug delivery, self-assembling materials, and stimuli-responsive systems.
Used in Rod-Coil Polymers:
4-Bromobenzyl alcohol is used as a monomer in the synthesis of symmetric rod-coil block copolymers, which are composed of rigid rod-like and flexible coil-like segments. These copolymers have potential applications in the formation of self-assembled nanostructures, such as micelles, vesicles, and hydrogels, for use in drug delivery, tissue engineering, and other advanced materials.
Used in Triblock Copolymers:
4-Bromobenzyl alcohol is used as a monomer in the synthesis of triblock copolymers of poly(9,9-didodecylfluorene-2,7-diyl) and poly(hydroxyl ethyl methacrylate). These copolymers have potential applications in the development of advanced materials with unique properties, such as self-healing materials, stimuli-responsive materials, and materials with tailored mechanical properties.
Chemical Properties:
4-Bromobenzyl alcohol is a white to slightly beige crystalline powder or crystals, which indicates its solid-state nature and purity. Its chemical properties make it suitable for various synthetic applications and reactions, contributing to its wide range of uses in the chemical and materials science industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3074, 1983 DOI: 10.1021/jo00166a029Tetrahedron Letters, 36, p. 3169, 1995 DOI: 10.1016/0040-4039(95)00504-6

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 873-75-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 873-75:
(5*8)+(4*7)+(3*3)+(2*7)+(1*5)=96
96 % 10 = 6
So 873-75-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H7BrO/c8-7-3-1-6(5-9)2-4-7/h1-4,9H,5H2

873-75-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A13197)  4-Bromobenzyl alcohol, 99%   

  • 873-75-6

  • 10g

  • 450.0CNY

  • Detail
  • Alfa Aesar

  • (A13197)  4-Bromobenzyl alcohol, 99%   

  • 873-75-6

  • 50g

  • 1884.0CNY

  • Detail

873-75-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Bromobenzyl alcohol

1.2 Other means of identification

Product number -
Other names p-Br benzyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:873-75-6 SDS

873-75-6Synthetic route

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With hydrogen; Et4N In 1,2-dimethoxyethane at 100℃; under 38000 Torr; for 13h;100%
With tri-n-butyl-tin hydride In methanol; diethyl ether for 4h; Reduction; Heating;100%
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h;100%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene 1.) 10-20 deg C, 2.) room temperature, 10 min;100%
With diisobutylaluminium hydride In toluene at 0℃; for 0.5h; Inert atmosphere;98%
Stage #1: 4-methoxycarbonylphenyl bromide With diethylzinc; lithium chloride In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere;
Stage #2: With sodium hydroxide In tetrahydrofuran; hexane; water at 20℃; for 8h; Inert atmosphere; chemoselective reaction;
98%
C28H24BBr4O4(1-)*Na(1+)

C28H24BBr4O4(1-)*Na(1+)

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With water100%
2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran
17100-68-4

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In methanol99.8%
With sulfuric acid; silica gel In methanol at 20℃; for 0.5h;98%
With trichloroisocyanuric acid In methanol at 20℃; for 4h;95%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;98%
With LiPh2InH2 In diethyl ether for 24h; Ambient temperature;95%
Stage #1: Ethyl 4-bromobenzoate With trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; 1-Phenylbut-1-en-3-one In dichloromethane at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; Inert atmosphere;
Stage #3: With potassium carbonate In methanol; hexane; dichloromethane at 20℃; for 0.5h; Inert atmosphere;
93%
(4-bromobenzyloxy)trimethylsilane
86605-93-8

(4-bromobenzyloxy)trimethylsilane

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry;98%
With rice husk ash supported on anatase-phase titania nanoparticles nanocomposite In methanol at 20℃; for 0.05h;97%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.0666667h;96%
4-bromobenzyl acetate
21388-92-1

4-bromobenzyl acetate

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With magnesium methanolate In methanol Ambient temperature;96%
With water at 20℃; for 0.416667h;96%
With potassium hydroxide
1-bromo-4-[(methoxymethyloxy)methyl]benzene
130534-91-7

1-bromo-4-[(methoxymethyloxy)methyl]benzene

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0166667h; Microwave irradiation; chemoselective reaction;96%
With bismuth(III) chloride; water In acetonitrile at 50℃; for 10h;88%
With niobium pentachloride In acetonitrile at 0 - 20℃; for 1h;81%
phosphotungstic acid In ethanol for 6h; Heating;73%
4-bromo-1-[(ethoxymethoxy)methyl]benzene
216443-67-3

4-bromo-1-[(ethoxymethoxy)methyl]benzene

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0166667h; Microwave irradiation; chemoselective reaction;95%
phosphotungstic acid In ethanol for 5.5h; Heating;82%
(E)-6-(4-bromobenzyloxy)hex-3-en-2-one
1140924-37-3

(E)-6-(4-bromobenzyloxy)hex-3-en-2-one

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 22℃; for 1h;94%
4-(tert-butyldimethylsiloxymethyl)bromobenzene
87736-74-1

4-(tert-butyldimethylsiloxymethyl)bromobenzene

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With potassium hydrogen difluoride In methanol at 60℃; for 16h;94%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
Stage #1: 4-Bromobenzoic acid With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Inert atmosphere;
Stage #2: With silica gel In methanol at 50℃; for 3h;
93%
Stage #1: 4-Bromobenzoic acid With sodium aminodiboranate In tetrahydrofuran at 20℃;
Stage #2: With water
90%
With potassium borohydride; hafnium tetrachloride In tetrahydrofuran at 40℃; for 18.6h; Inert atmosphere; Cooling with ice;84%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

A

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

B

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
Stage #1: 4-bromo-benzaldehyde With potassium hydroxide for 0.0833333h; Cannizzaro Reaction; Milling; Inert atmosphere; Sealed tube; Green chemistry;
Stage #2: With hydrogenchloride In water Green chemistry;
A 92%
B 92%
With sodium hydroxide In water at 15℃; for 3h; Cannizzaro Reaction;A 90%
B n/a
With [(hydrotris(3,5-diphenylpyrazole-1-yl)borate)-FeII(benzilate)]; oxygen In benzene at 20℃; Inert atmosphere;A 85%
B 40%
C13H13BrOSi

C13H13BrOSi

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With sodium hydroxide In water Schlenk technique; Inert atmosphere;92%
With sodium hydroxide In water
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With potassiumhexacyanoferrate(II) trihydrate; C30H27FeN2OP; water; palladium diacetate; sodium carbonate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Schlenk technique;90%
With oxygen; eosin y In dimethyl sulfoxide at 25℃; for 12h; Irradiation;81%
With lead(II) oxide; acetic acid Behandeln des Reaktionsprodukts mit methanol. KOH;
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

A

para-bromotoluene
106-38-7

para-bromotoluene

B

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

C

benzaldehyde
100-52-7

benzaldehyde

D

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In water; isopropyl alcohol at 20℃; under 724.026 Torr; for 16h;A 4%
B 90%
C 1%
D 4%
2-((4-bromobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1566593-61-0

2-((4-bromobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With water; silica gel In methanol at 60℃; Inert atmosphere;90%
With hydrogenchloride In tetrahydrofuran; methanol; water at 50℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;87%
With silica gel In methanol at 60℃; for 3h; Inert atmosphere;83%
p-bromobenzaldehyde tosylhydrazone
19350-68-6

p-bromobenzaldehyde tosylhydrazone

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With water; potassium carbonate at 130℃; for 0.166667h; Microwave irradiation;89%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃;88%
With sulfuric acid; hydrogen; nickel In tetrahydrofuran
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

glycerol
56-81-5

glycerol

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With C27H31ClN3RuSe(1+)*F6P(1-); potassium hydroxide In water at 110℃; for 6h; Reagent/catalyst; Time;88%
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

butan-1-ol
71-36-3

butan-1-ol

A

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

B

1-bromo-4-(butoxymethyl)benzene
133842-36-1

1-bromo-4-(butoxymethyl)benzene

Conditions
ConditionsYield
With sodium hydroxide; 5,11,17,23-tetramethoxy-25,26,27,28-tetrakis(trimethylammoniomethyl)calix<4>arene tetrachloride at 60℃; for 2h;A 3%
B 87%
4-bromo-N,N-dimethylbenzamide
18469-37-9

4-bromo-N,N-dimethylbenzamide

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With sodium hydride; sodium iodide; zinc(II) iodide In tetrahydrofuran; mineral oil at 40℃; for 7h; Sealed tube;87%
2-(4-bromophenyl)-1,3-oxathiolane
147441-51-8, 147441-52-9, 77853-37-3

2-(4-bromophenyl)-1,3-oxathiolane

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 2h;86%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

B

2-((4-bromobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1566593-61-0

2-((4-bromobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With tris(cyclopentadienyl)lanthanum(III) In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;A 86%
B n/a
p-bromobenzamide
698-67-9

p-bromobenzamide

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;86%
With [fac-8-(2-diphenylphosphinoethyl)aminotrihydroquinoline]RuH(η1-BH4)(CO); hydrogen In isopropyl alcohol at 140℃; under 37503.8 Torr; for 24h; Autoclave;60 %Chromat.
4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In various solvent(s) at 80℃; for 3h;84%
With aluminum oxide; sodium tetrahydroborate In diethyl ether
With lithium aluminium tetrahydride In diethyl ether
(4-bromophenyl)methylenediacetate
55605-27-1

(4-bromophenyl)methylenediacetate

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 20℃; for 2h; chemoselective reaction;84%
formaldehyd
50-00-0

formaldehyd

4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With C62H74Cl2N4Pd2S2; caesium carbonate In tetrahydrofuran; water at 50℃; for 2h; Inert atmosphere; Sealed tube;83%
With di-μ-chloro-bis{2-[3-(2,6-diisopropylphenyl)imidazolin-2-ylidene]-(3-phenylthio)phenyl-κ2C,C’}dipalladium(II); caesium carbonate In tetrahydrofuran; water at 70℃; for 2h; Inert atmosphere; Sealed tube;75%
With rhodium(III) chloride; triphenylphosphine; sodium hydroxide In tetrahydrofuran at 130℃; for 6h; Autoclave; Inert atmosphere;71%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

A

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

B

2,2-bis(4-bromophenyl)ethanol
1007224-79-4

2,2-bis(4-bromophenyl)ethanol

Conditions
ConditionsYield
With zinc In water at 90 - 160℃; for 2h; Microwave irradiation; Green chemistry;A 15%
B 83%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With dinitrogen tetraoxide; ferric nitrate for 0.08h; Ambient temperature; further oxidizing agent, further conditions and solvents;100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.333333h; Heating;100%
With 1H-imidazole; sodium periodate; manganese(III)-porphyrin complex immobilized on polystyrene In water; acetonitrile at 20℃; for 0.75h;100%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-(tert-butyldimethylsiloxymethyl)bromobenzene
87736-74-1

4-(tert-butyldimethylsiloxymethyl)bromobenzene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;100%
With 1H-imidazole In dichloromethane at 20℃; for 12h;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 72h;100%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

acetic anhydride
108-24-7

acetic anhydride

4-bromobenzyl acetate
21388-92-1

4-bromobenzyl acetate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 5 - 30℃; for 15.13h;100%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.0833333h;99%
K5 In acetonitrile at 20℃; for 0.25h;99%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

(4-bromobenzyloxy)trimethylsilane
86605-93-8

(4-bromobenzyloxy)trimethylsilane

Conditions
ConditionsYield
With 1-adamanthanol; N,N'-dibromo-N,N'-1,2-ethanediylbis-(benzenesulfonamide) In dichloromethane at 20℃; for 2h;100%
With tribromomelamine In dichloromethane; acetonitrile at 20℃; for 1.25h;98%
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry;98%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

2-Biphenylboronic acid
4688-76-0

2-Biphenylboronic acid

[1,1':2',1
6051-49-6

[1,1':2',1"-terphenyl]-4-ylmethanol

Conditions
ConditionsYield
With dichlorido[2-(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)pyridine]palladium(II); potassium carbonate In ethanol; water for 0.5h; Suzuki-Miyaura Coupling; Reflux;100%
With palladium diacetate; potassium carbonate; triphenylphosphine In water; toluene at 110℃; Sealed tube;85%
2-Methoxypropene
116-11-0

2-Methoxypropene

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-bromo-1-(1-methoxy-1-methylethoxymethyl)benzene
1201913-76-9

4-bromo-1-(1-methoxy-1-methylethoxymethyl)benzene

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In tetrahydrofuran at -20℃; for 15h; Inert atmosphere;100%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

nitrobenzene
98-95-3

nitrobenzene

A

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

B

N-(4-bromobenzylidene)aniline
5877-51-0

N-(4-bromobenzylidene)aniline

Conditions
ConditionsYield
With α,α,α-trifluorotoluene; titanium(IV) oxide In dodecane under 750.075 Torr; for 3h; Darkness; Inert atmosphere; Irradiation;A n/a
B 100%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

1,3-diallyl-6-chloro-1,3,5-triazine-2,4(1H,3H)-dione

1,3-diallyl-6-chloro-1,3,5-triazine-2,4(1H,3H)-dione

1,3-diallyl-6-(4-bromobenzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione

1,3-diallyl-6-(4-bromobenzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; triethylamine In tetrahydrofuran at 0 - 20℃;100%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

aniline
62-53-3

aniline

N-(4-bromobenzylidene)aniline
5877-51-0

N-(4-bromobenzylidene)aniline

Conditions
ConditionsYield
With potassium hydroxide In toluene at 50℃; for 0.666667h; Molecular sieve;99.9%
With C30H24AgBr4N8(1+)*AgBr2(1-); N-benzyl-trimethylammonium hydroxide In toluene at 20℃; for 12h; Molecular sieve; Schlenk technique;98%
With oxygen In toluene at 80℃; for 24h; Schlenk technique;97%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran
17100-68-4

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In acetonitrile for 0.166667h;99.7%
Stage #1: 3,4-dihydro-2H-pyran; 4-bromobenzenemethanol With toluene-4-sulfonic acid In dichloromethane at 20℃; for 96h;
Stage #2: With potassium carbonate In dichloromethane for 2h;
98%
In dichloromethane at 20℃; for 0.133333h;98%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
ConditionsYield
With bromine; triphenylphosphine In dichloromethane at -78 - 20℃; for 18h; Inert atmosphere;99%
With 1,1,1,2,2,2-hexamethyldisilane In chloroform for 2h; Reflux;98%
With phosphorus tribromide In chloroform at 0 - 20℃; for 1h;94%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

methyl iodide
74-88-4

methyl iodide

1-bromo-4-methoxymethylbenzene
1515-88-4

1-bromo-4-methoxymethylbenzene

Conditions
ConditionsYield
Stage #1: 4-bromobenzenemethanol With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 1h;
Stage #2: methyl iodide In tetrahydrofuran; paraffin oil at 20℃; for 15h;
99%
Stage #1: 4-bromobenzenemethanol With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1h;
Stage #2: methyl iodide In dimethyl sulfoxide for 0.166667h;
99%
With potassium hydroxide In dimethyl sulfoxide for 0.5h; Ambient temperature;96%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-(triisopropylsilyloxymethyl)bromobenzene
181717-64-6

4-(triisopropylsilyloxymethyl)bromobenzene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;99%
With 1H-imidazole In N,N-dimethyl-formamide at 21℃; for 1h;91%
With 1H-imidazole In N,N-dimethyl-formamide
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

formic acid ethyl ester
109-94-4

formic acid ethyl ester

4-tert-butylbenzyl formate

4-tert-butylbenzyl formate

Conditions
ConditionsYield
With tribromomelamine In neat (no solvent) at 20℃; for 1h; Time; Solvent; Green chemistry; chemoselective reaction;99%
With K5 for 0.75h; Heating;98%
With bismuth(lll) trifluoromethanesulfonate for 0.5h; Heating;96%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

(4-bromobenzyl)-2,2,2-trichloroacetimidate
146285-52-1

(4-bromobenzyl)-2,2,2-trichloroacetimidate

Conditions
ConditionsYield
Stage #1: 4-bromobenzenemethanol With sodium hydride In tetrahydrofuran; mineral oil at 25℃; Inert atmosphere;
Stage #2: trichloroacetonitrile In tetrahydrofuran; mineral oil at 0 - 25℃; Inert atmosphere;
99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexane at 0℃; for 0.5h;95%
Stage #1: 4-bromobenzenemethanol With sodium hydride In diethyl ether; oil at 20℃; for 0.0833333h;
Stage #2: trichloroacetonitrile In diethyl ether; oil at 20℃; for 2h;
92%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h;84%
Stage #1: 4-bromobenzenemethanol In toluene for 0.333333h; Metallation;
Stage #2: trichloroacetonitrile at 20℃; for 1h; Addition;
25%
carbon disulfide
75-15-0

carbon disulfide

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

methyl iodide
74-88-4

methyl iodide

O-4-bromophenylmethyl S-methyl dithiocarbonate

O-4-bromophenylmethyl S-methyl dithiocarbonate

Conditions
ConditionsYield
Stage #1: carbon disulfide; 4-bromobenzenemethanol With sodium hydride In tetrahydrofuran at 20℃; for 10h; Addition;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Methylation;
99%
Stage #1: 4-bromobenzenemethanol With sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: carbon disulfide In tetrahydrofuran at 0℃; for 0.166667h;
Stage #3: methyl iodide In tetrahydrofuran at 0 - 20℃;
88%
Stage #1: 4-bromobenzenemethanol With 1H-imidazole; sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: carbon disulfide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
82%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

benzoic acid anhydride
93-97-0

benzoic acid anhydride

4-bromobenzyl benzoate
38612-13-4

4-bromobenzyl benzoate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.5h; Heating;99%
methanol
67-56-1

methanol

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

Conditions
ConditionsYield
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h;99%
With potassium carbonate at 60℃; under 750.075 Torr; for 2h;94.1%
With oxygen at 70℃; under 750.075 Torr; for 16h;93%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

Conditions
ConditionsYield
Stage #1: 4-bromobenzenemethanol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
99%
With ammonium hydroxide; oxygen In tert-Amyl alcohol under 7500.75 Torr; for 16h; Green chemistry;99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 4h; Autoclave; High pressure;99%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-bromobenzyliodide
55883-45-9

4-bromobenzyliodide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; iodine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 20℃; under 22502.3 Torr; Autoclave; Schlenk technique;99%
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; Ru(OCOCH3)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; hydrogen; iodine In toluene at 20℃; under 22502.3 Torr; for 10.5h;99%
Stage #1: 4-bromobenzenemethanol With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane
Stage #2: With potassium iodide In dichloromethane; N,N-dimethyl-formamide for 0.1h;
96%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl-4-yl methanol
3597-91-9

biphenyl-4-yl methanol

Conditions
ConditionsYield
With C20H20N2O2Pd; sodium hydrogencarbonate In water at 80℃; for 6h; Suzuki-Miyaura Coupling;99%
With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium carbonate In water for 0.5h; Catalytic behavior; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; Reflux;98%
With palladium diacetate; potassium carbonate; urea In water; isopropyl alcohol at 20℃; for 0.333333h; Suzuki-Miyaura Coupling; Green chemistry;97%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

methanesulfonic acid 4-bromo-benzyl ester
237763-11-0

methanesulfonic acid 4-bromo-benzyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -20 - 20℃; for 3h;99%
With triethylamine In dichloromethane at -50℃; for 0.5h;99%
Stage #1: 4-bromobenzenemethanol With triethylamine In tetrahydrofuran at 0℃;
Stage #2: methanesulfonyl chloride In tetrahydrofuran at 0 - 20℃;
74%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4-(hydroxymethyl)-1-(trimethylsilylethynyl)benzene
275386-60-2

4-(hydroxymethyl)-1-(trimethylsilylethynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 23h; Inert atmosphere;99%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 70℃; for 36h; Sonogashira Cross-Coupling;93%
With copper(l) iodide; triethylamine; bis(triphenylphosphine)palladium(II)-chloride at 70℃; for 36h;92%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

(4'-methyl-[1,1'-biphenyl]-4-yl)methanol

(4'-methyl-[1,1'-biphenyl]-4-yl)methanol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; ammonium bicarbonate In water at 100℃; for 24h; Time; Suzuki Coupling; Inert atmosphere; Schlenk technique;99%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol Suzuki cross-coupling; microwave irradiation;89%
1H-imidazole
288-32-4

1H-imidazole

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-(tert-butyldimethylsiloxymethyl)bromobenzene
87736-74-1

4-(tert-butyldimethylsiloxymethyl)bromobenzene

Conditions
ConditionsYield
In N,N-dimethyl-formamide99%
In dichloromethane
1H-imidazole
288-32-4

1H-imidazole

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

1-(Hydroxymethyl)-4-(1H-imidazol-1-yl)benzene
86718-08-3

1-(Hydroxymethyl)-4-(1H-imidazol-1-yl)benzene

Conditions
ConditionsYield
With copper(I) oxide; potassium phosphate; N1,N2-bis(furan-2-ylmethyl)oxalamide In dimethyl sulfoxide at 120℃; for 24h;99%
With 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;80%
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; tetrabutylammomium bromide; sodium hydroxide In water at 120℃; for 48h; Inert atmosphere;79%

873-75-6Relevant articles and documents

Green synthesis of metal oxide nanoparticles and their catalytic activity for the reduction of aldehydes

Muthuvinothini,Stella

, p. 48 - 56 (2019)

In the present work, a green synthesis of Metal Oxide nanoparticles was demonstrated using the freshly prepared aqueous extract of the immature fruit of Cocos nucifera and the MO nanoparticles were characterized by the analytical techniques such as UV–vis, FT-IR, XRD, SEM, TEM and EDAX. Characterization techniques confirmed that the biomolecules involved in the formation of nanoparticles and also they stabilized the nanoparticles. The synthesized MO nanoparticles were used as catalysts for the reduction of aromatic aldehydes. The reduction was done at mild reaction conditions using ammonium formate as a green hydrogen donor and the corresponding alcohols were obtained in 2–24 h with excellent yields. The reduction reaction was optimized using various solvents, loading of catalyst and at different temperatures.

Hydrogenation of Esters by Manganese Catalysts

Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin

, (2022/01/13)

The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).

BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage

Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh

supporting information, p. 7109 - 7116 (2021/05/03)

A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.

Hydrosilylation of Aldehydes and Ketones Catalyzed by a 2-Iminopyrrolyl Alkyl-Manganese(II) Complex

Cruz, Tiago F. C.,Gomes, Pedro T.,Veiros, Luís F.

, (2022/01/11)

A well-defined and very active single-component manganese(II) catalyst system for the hydrosilylation of aldehydes and ketones is presented. First, the reaction of 5-(2,4,6-iPr3C6H2)-2-[N-(2,6-iPr2C6H3)formimino]pyrrolyl potassium (KL) and [MnCl2(Py)2] afforded the binuclear 2-iminopyrrolyl manganese(II) pyridine chloride complex [Mn2{κ2N,N′-5-(2,4,6-iPr3C6H2)-NC4H2-2-C(H)═N(2,6-iPr2C6H3)}2(Py)2(μ-Cl)2] 1. Subsequently, the alkylation reaction of complex 1 with LiCH2SiMe3 afforded the respective (trimethylsilyl)methyl-Mn(II) complex [Mn{κ2N,N′-5-(2,4,6-iPr3C6H2)-NC4H2-2-C(H)═N(2,6-iPr2C6H3)}(Py)CH2SiMe3] 2 in a good yield. Complexes 1 and 2 were characterized by elemental analysis, 1H NMR spectroscopy, Evans' method, FTIR spectroscopy, and single-crystal X-ray diffraction. While the crystal structure of complex 1 has been identified as a binuclear entity, in which the Mn(II) centers present pentacoordinate coordination spheres, that of complex 2 corresponds to a monomer with a distorted tetrahedral coordination geometry. Complex 2 proved to be a very active precatalyst for the atom-economic hydrosilylation of several aldehydes and ketones under very mild conditions, with a maximum turnover frequency of 95 min-1, via a silyl-Mn(II) mechanistic route, as asserted by a combination of experimental and theoretical efforts, the respective silanes were cleanly converted to the respective alcoholic products in high yields.

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